366800-07-9

Upstream product

• 173043-70-4 (E)-2-nonen-8-yn-1-ol 
• 824-94-2 p-methoxybenzyl chloride 
• 79439-15-9 methyl trans-2-nonen-8-ynoate 

Downstream Products

• 366800-08-0 (2S,3S)-1-[(4-methoxybenzyl)oxy]non-8-yne-2,3-diol 
• 366800-25-1 2-[(E)-(7S,8S)-7-Allyloxy-8-hydroxy-9-(4-methoxy-benzyloxy)-non-1-enyl]-6-methoxy-benzoic acid 
• 366800-26-2 2-[(E)-(7S,8S)-8-Allyloxy-7-hydroxy-9-(4-methoxy-benzyloxy)-non-1-enyl]-6-methoxy-benzoic acid 
• 366800-17-1 2-[(E)-(7S,8S)-7-Allyloxy-8-hydroxy-9-(4-methoxy-benzyloxy)-non-1-enyl]-6-methoxy-benzoic acid methyl ester 
• 366800-18-2 2-[(E)-(7S,8S)-8-Allyloxy-7-hydroxy-9-(4-methoxy-benzyloxy)-non-1-enyl]-6-methoxy-benzoic acid methyl ester 
• 366800-16-0 methyl 2-{(1E,7S,8S)-7,8-dihydroxy-9-[(4-methoxybenzyl)oxy]non-1-enyl}-6-methoxybenzoate 
• 366800-13-7 2-{(1E,7S,8S)-7,8-dihydroxy-9-[(4-methoxybenzyl)oxy]non-1-enyl}-6-methoxybenzoic acid 
• 366800-12-6 methyl 2-methoxy-6-{(1E)-6-[(4S,5S)-5-{[(4-methoxybenzyl)oxy]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]hex-1-enyl}benzoate 
• 366800-09-1 (4S,5S)-4-(hex-5-ynyl)-5-{[(4-methoxybenzyl)oxy]methyl}-2,2-dimethyl-2,3-dioxolane 

Relevant academic research and scientific papers

Synthesis of a model system for the macrocyclic subunit of the oximidines

Cross-coupling reaction of aryl triflate 1 and vinyl stannane 13 provided salicylic acid derivative 15. This compound was converted to the dihydroxy acid 16, which provided in a size-selective macrolactonization the two macrolides 17 and 18 in a ratio of 60:40. Compound 17 is a model of the macrocyclic core of the oximidines.

Applications of size-selective macrolactonizations to the synthesis of benzolactone-enamide core structures

By utilizing Stille cross-coupling reactions four benzoic acid derivatives (18, 32, 46, 66) were prepared that carry a side chain with two secondary hydroxy groups. It could be shown that the hydroxy functions can be distinguished by size-selective macrolactonization reactions. Thus, 12-membered lactones 19 and 33 are favored over their 11-membered lactone counterparts 20 and 34, respectively, albeit with a low (60:40-70:30) ratio. The selectivity is much more pronounced if there is a competition between a 12- and 10-membered lactone. This could be shown with the two lactones 47 and 67. The 12-membered lactones 33, 47, and 67 represent core structures for analogs of the benzolactone enamides. The macrolactonization reactions were performed under Yamaguchi conditions.